AR034869A1 - PROCEDURE FOR THE QUICK SYNTHESIS OF A PEPTIDE IN SOLUTION, METHODS FOR THE COMBINATORY SYNTHESIS OF LIBRARY LIBRARIES AND FOR THE AUTOMATED SYNTHESIS OF PEPTIDES IN SOLUTION THAT APPLY SUCH PROCEDURE AND A PEPTIDE OR A MATCH - Google Patents
PROCEDURE FOR THE QUICK SYNTHESIS OF A PEPTIDE IN SOLUTION, METHODS FOR THE COMBINATORY SYNTHESIS OF LIBRARY LIBRARIES AND FOR THE AUTOMATED SYNTHESIS OF PEPTIDES IN SOLUTION THAT APPLY SUCH PROCEDURE AND A PEPTIDE OR A MATCHInfo
- Publication number
- AR034869A1 AR034869A1 ARP020102687A ARP020102687A AR034869A1 AR 034869 A1 AR034869 A1 AR 034869A1 AR P020102687 A ARP020102687 A AR P020102687A AR P020102687 A ARP020102687 A AR P020102687A AR 034869 A1 AR034869 A1 AR 034869A1
- Authority
- AR
- Argentina
- Prior art keywords
- peptide
- synthesis
- procedure
- solution
- peptides
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
Abstract
Un procedimiento para la síntesis rápida de un péptido en solución, que comprende ciclos repetidos de las etapas (a) - (d): (a) una etapa de acoplamiento usando un exceso de un componente carboxílico activado para acilar un componente amino, (b) una etapa de extinción en que se usa un agente barredor para remover las funciones carboxílicas activadas residuales, done el agente barredor también puede usarse para la desprotección del péptido en crecimiento. (c) una o más extracciones acuosas y opcionalmente, (d) una etapa de desprotección separada, seguida por una o más extracciones acuosas, en donde el procedimiento comprende al menos una etapa (b), denominada etapa (b'), en que una amina o un tiol que comprende un anión libre o un anión latente se usa como agente barredor de las funciones carboxílicas activadas residuales. El anión latente en la amina barredora lleva un grupo protector temporal, de tipo bencilo, más específicamente un derivado de aminoácido protegido en el c-terminal, tal como la beta-alanina. El agente barredor es beta-alaninato de bencilo, un tiol que comprende un anión libre o latente o una poliamina. El procedimiento comprende extracciones que se efectúan en presencia de cloruro de sodio o nitrato de potasio. Durante el procedimiento el péptido en crecimiento no necesita ser aislado hasta que se haya obtenido la secuencia final del péptido. Este procedimiento altamente eficiente es útil para la producción de oligo- y polipéptidos de alta pureza. También se divulgan métodos para la síntesis combinatoria de bibliotecas de péptidos y para la síntesis automatizada de péptidos en solución que aplican el procedimiento y un péptido o una mezcla de péptidos así obtenido (a).A method for rapid synthesis of a peptide in solution, comprising repeated cycles of steps (a) - (d): (a) a coupling step using an excess of an activated carboxylic component to acylate an amino component, (b ) an extinction step in which a sweeping agent is used to remove residual activated carboxylic functions, where the sweeping agent can also be used for deprotection of the growing peptide. (c) one or more aqueous extractions and optionally, (d) a separate deprotection stage, followed by one or more aqueous extractions, wherein the process comprises at least one stage (b), called stage (b '), in which an amine or a thiol comprising a free anion or a latent anion is used as a sweeping agent for residual activated carboxylic functions. The latent anion in the sweeping amine carries a temporary, benzyl-like protecting group, more specifically a c-terminal protected amino acid derivative, such as beta-alanine. The sweeping agent is benzyl beta-alaninate, a thiol comprising a free or latent anion or a polyamine. The process comprises extractions that are carried out in the presence of sodium chloride or potassium nitrate. During the procedure the growing peptide does not need to be isolated until the final sequence of the peptide has been obtained. This highly efficient procedure is useful for the production of oligo- and high purity polypeptides. Methods for combinatorial synthesis of peptide libraries and for automated synthesis of peptides in solution that apply the procedure and a peptide or a mixture of peptides thus obtained are also disclosed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01202753 | 2001-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR034869A1 true AR034869A1 (en) | 2004-03-24 |
Family
ID=8180656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020102687A AR034869A1 (en) | 2001-07-19 | 2002-07-18 | PROCEDURE FOR THE QUICK SYNTHESIS OF A PEPTIDE IN SOLUTION, METHODS FOR THE COMBINATORY SYNTHESIS OF LIBRARY LIBRARIES AND FOR THE AUTOMATED SYNTHESIS OF PEPTIDES IN SOLUTION THAT APPLY SUCH PROCEDURE AND A PEPTIDE OR A MATCH |
Country Status (26)
| Country | Link |
|---|---|
| US (4) | US20030018164A1 (en) |
| EP (1) | EP1291356B1 (en) |
| JP (1) | JP4142907B2 (en) |
| KR (1) | KR100861031B1 (en) |
| CN (1) | CN1254483C (en) |
| AR (1) | AR034869A1 (en) |
| AT (1) | ATE302792T1 (en) |
| BR (1) | BRPI0202783B1 (en) |
| CA (1) | CA2390358C (en) |
| DE (1) | DE60205693T2 (en) |
| DK (1) | DK1291356T3 (en) |
| EC (1) | ECSP024291A (en) |
| ES (1) | ES2248485T3 (en) |
| HK (1) | HK1050904A1 (en) |
| HR (1) | HRP20020609B1 (en) |
| HU (1) | HUP0202369A2 (en) |
| IL (1) | IL150601A (en) |
| MX (1) | MXPA02006998A (en) |
| NO (1) | NO324245B1 (en) |
| PE (1) | PE20030214A1 (en) |
| PL (1) | PL205559B1 (en) |
| PT (1) | PT1291356E (en) |
| RU (1) | RU2237673C2 (en) |
| SG (1) | SG119160A1 (en) |
| TW (1) | TWI247012B (en) |
| ZA (1) | ZA200205409B (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI247012B (en) * | 2001-07-19 | 2006-01-11 | Akzo Nobel Nv | Process for rapid solution synthesis of peptides |
| EP1790656A1 (en) | 2005-11-25 | 2007-05-30 | Nanokem S.A. | Solution-phase synthesis of leuprolide |
| EP1801086A1 (en) * | 2005-11-25 | 2007-06-27 | Synthacon GmbH | Synthesis of carbon acid amides |
| US20090093016A1 (en) * | 2006-01-17 | 2009-04-09 | N.V. Organon | Selective Enzymatic Hydrolysis of C-Terminal Tert-Butyl Esters of Peptides |
| US8716439B2 (en) | 2006-03-01 | 2014-05-06 | Kaneka Corporation | Method of producing peptide |
| US8124372B2 (en) | 2007-06-25 | 2012-02-28 | N.V. Organon | Selective enzymatic amidation of C-terminal esters or acids of peptides |
| MX2009013623A (en) * | 2007-06-25 | 2010-01-20 | Organon Nv | Process for the conversion of c-terminal peptide esters or acids to amides employing subtilisin in the presence of ammonium salts. |
| EP2235038B1 (en) * | 2008-12-30 | 2019-06-05 | GKL-Biotec AG | Tetrapeptide Combination |
| KR101032399B1 (en) * | 2010-02-11 | 2011-05-03 | 주식회사 이너트론 | Metal housing for bandpath filter and the manufacturing method thereof |
| EP2409982A3 (en) * | 2010-02-25 | 2012-02-08 | Corning Incorporated | Chemical processes generating solid(s) carried out continuously within microreactors |
| WO2013089241A1 (en) | 2011-12-15 | 2013-06-20 | 味の素株式会社 | METHOD FOR REMOVING Fmoc GROUP |
| DK3266792T3 (en) | 2015-03-04 | 2021-02-01 | Jitsubo Co Ltd | Method for peptide synthesis |
| ES2957399T3 (en) | 2018-04-13 | 2024-01-18 | Jitsubo Co Ltd | Peptide synthesis method |
| FR3090636B1 (en) * | 2018-12-24 | 2021-01-01 | Strainchem | Peptide Synthesis Process |
| CA3126705A1 (en) | 2019-02-01 | 2020-08-06 | Gap Peptides Llc | Synthesis strategy for gap protecting group |
| TW202138382A (en) * | 2019-12-27 | 2021-10-16 | 日商中外製藥股份有限公司 | Method for synthesizing peptide compound |
| WO2021192488A1 (en) * | 2020-03-27 | 2021-09-30 | 株式会社カネカ | Method for producing amide bond-containing compound |
| JP7063408B1 (en) | 2021-07-02 | 2022-05-09 | ペプチスター株式会社 | Liquid phase peptide production method |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1991A (en) * | 1841-02-23 | Manner of fastening bedsteads | ||
| US5221754A (en) * | 1989-06-09 | 1993-06-22 | Research Corporation Technologies, Inc. | Reagents for rapid peptide synthesis |
| US5101059A (en) * | 1989-12-05 | 1992-03-31 | Research Corporation Technologies, Inc. | Amino acid protecting groups |
| US5877278A (en) | 1992-09-24 | 1999-03-02 | Chiron Corporation | Synthesis of N-substituted oligomers |
| US5516892A (en) | 1992-12-28 | 1996-05-14 | Indiana University Foundation | Polymer-bound mixed carboxylic anhdrides as a stable form of activated carboxylic acids |
| US6310180B1 (en) * | 1993-06-21 | 2001-10-30 | Vanderbilt University | Method for synthesis of proteins |
| US5516639A (en) * | 1993-07-22 | 1996-05-14 | Mayo Foundation For Medical Education And Research | Antibodies specific for human prostate glandular kallkrein |
| US6001966A (en) | 1995-10-19 | 1999-12-14 | Proligo Llc | Method for solution phase synthesis of oligonucleotides and peptides |
| US5698676A (en) | 1995-11-30 | 1997-12-16 | Abbott Laboratories | Use of propylene oxide as an acid scavenger in peptide synthesis |
| US5849954A (en) * | 1996-01-18 | 1998-12-15 | Research Corporation Technologies, Inc. | Method of peptide synthesis |
| NZ332116A (en) | 1996-05-03 | 2000-06-23 | Warner Lambert Co | Rapid purification of synthetic intermediates and products by polymer supported quench reagents |
| US6121488A (en) * | 1997-09-24 | 2000-09-19 | Warner-Lambert Company | Quenching reagents for solution phase synthesis |
| JPH11217397A (en) * | 1997-11-27 | 1999-08-10 | Saburo Aimoto | Production of peptide thiol ester |
| FR2780061B1 (en) | 1998-06-22 | 2001-09-07 | Rhone Poulenc Rorer Sa | NOVEL PROCESS FOR THE PREPARATION OF CYCLOSPORIN DERIVATIVES |
| EP1180115A1 (en) * | 1999-05-26 | 2002-02-20 | Abbott Laboratories | Minimal isolation peptide synthesis process using ion-exchange resins as scavenging agents |
| US20020127219A1 (en) | 1999-12-30 | 2002-09-12 | Okkels Jens Sigurd | Lysosomal enzymes and lysosomal enzyme activators |
| US7205120B2 (en) | 2000-07-19 | 2007-04-17 | Pharmacia & Upjohn Company | Substrates and assays for β-secretase activity |
| IL150600A (en) * | 2001-07-19 | 2005-09-25 | Akzo Nobel Nv | Process for the preparation of compounds containing one or more amide bonds using an excess of an activated carboxylic component and scavenging the residual activated carboxylic component |
| TWI247012B (en) * | 2001-07-19 | 2006-01-11 | Akzo Nobel Nv | Process for rapid solution synthesis of peptides |
| US20060287485A1 (en) * | 2005-06-17 | 2006-12-21 | Crawford Emmett D | Sound barriers comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
-
2002
- 2002-07-04 TW TW091114832A patent/TWI247012B/en not_active IP Right Cessation
- 2002-07-04 IL IL150601A patent/IL150601A/en active IP Right Grant
- 2002-07-05 JP JP2002197550A patent/JP4142907B2/en not_active Expired - Lifetime
- 2002-07-05 ZA ZA200205409A patent/ZA200205409B/en unknown
- 2002-07-15 EP EP02077830A patent/EP1291356B1/en not_active Expired - Lifetime
- 2002-07-15 ES ES02077830T patent/ES2248485T3/en not_active Expired - Lifetime
- 2002-07-15 DE DE60205693T patent/DE60205693T2/en not_active Expired - Lifetime
- 2002-07-15 PT PT02077830T patent/PT1291356E/en unknown
- 2002-07-15 SG SG200204298A patent/SG119160A1/en unknown
- 2002-07-15 AT AT02077830T patent/ATE302792T1/en active
- 2002-07-15 DK DK02077830T patent/DK1291356T3/en active
- 2002-07-17 PE PE2002000637A patent/PE20030214A1/en not_active Application Discontinuation
- 2002-07-17 MX MXPA02006998A patent/MXPA02006998A/en active IP Right Grant
- 2002-07-18 CA CA002390358A patent/CA2390358C/en not_active Expired - Lifetime
- 2002-07-18 KR KR1020020041898A patent/KR100861031B1/en not_active IP Right Cessation
- 2002-07-18 RU RU2002119630/04A patent/RU2237673C2/en not_active IP Right Cessation
- 2002-07-18 AR ARP020102687A patent/AR034869A1/en active IP Right Grant
- 2002-07-18 CN CNB021261911A patent/CN1254483C/en not_active Expired - Lifetime
- 2002-07-18 HU HU0202369A patent/HUP0202369A2/en unknown
- 2002-07-18 NO NO20023446A patent/NO324245B1/en not_active IP Right Cessation
- 2002-07-18 BR BRPI0202783A patent/BRPI0202783B1/en active IP Right Grant
- 2002-07-19 PL PL355125A patent/PL205559B1/en not_active IP Right Cessation
- 2002-07-19 US US10/199,805 patent/US20030018164A1/en not_active Abandoned
- 2002-07-19 HR HR20020609A patent/HRP20020609B1/en not_active IP Right Cessation
- 2002-07-19 EC EC2002004291A patent/ECSP024291A/en unknown
-
2003
- 2003-04-29 HK HK03103037A patent/HK1050904A1/en not_active IP Right Cessation
- 2003-10-22 US US10/692,354 patent/US20040082760A1/en not_active Abandoned
- 2003-10-23 US US10/693,802 patent/US7435791B2/en not_active Expired - Lifetime
- 2003-10-23 US US10/693,123 patent/US20060063918A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AR034869A1 (en) | PROCEDURE FOR THE QUICK SYNTHESIS OF A PEPTIDE IN SOLUTION, METHODS FOR THE COMBINATORY SYNTHESIS OF LIBRARY LIBRARIES AND FOR THE AUTOMATED SYNTHESIS OF PEPTIDES IN SOLUTION THAT APPLY SUCH PROCEDURE AND A PEPTIDE OR A MATCH | |
| Albericio | Orthogonal protecting groups for Nα‐amino and C‐terminal carboxyl functions in solid‐phase peptide synthesis | |
| KR900009697A (en) | Peptide derivatives | |
| JP2002505672A (en) | Solid-phase natural chemical ligation of unprotected or N-terminal cysteine protected peptides in aqueous solution | |
| JP2011001384A (en) | Microwave enhanced n-fmoc deprotection in peptide synthesis | |
| JP7411414B2 (en) | Method for producing peptide and method for treating base | |
| ES2374389T3 (en) | PEPTIDE PREPARATION PROCEDURE. | |
| DE60123125D1 (en) | PROCESS FOR THE PREPARATION OF 1- (AMINOMETHYL) CYCLOHEXANIC ACID | |
| JP2899430B2 (en) | Sulfonate, sulfate, phosphonate, and phosphate derivatives of stabilized hirudin | |
| Hibino et al. | Synthesis and application of Nα‐Fmoc‐Nπ‐4‐methoxybenzyloxymethylhistidine in solid phase peptide synthesis | |
| DE602004023827D1 (en) | ION CHANNEL ACTIVITY INHIBITABLE LOW-MOLECULAR PEPTIDES | |
| WEN et al. | A systematic approach to the solid‐phase synthesis of linear and cyclic pseudopeptide libraries containing ψ [CH2NH] amide bond surrogates | |
| Spetzler et al. | Preparation and application of O‐amino‐serine, Ams, a new building block in chemoselective ligation chemistry | |
| JPH05508850A (en) | anticoagulant peptide | |
| JP2001505578A (en) | Peptide synthesis using sulfonyl protecting groups | |
| JPS6393796A (en) | Agent for eliminating protecting group in peptide synthesis | |
| EA200400603A1 (en) | NEW PEPTIDES - HORMONAL ANALOGUES FOR HUMAN GROWTH HORMONE GROWTH | |
| Johnson et al. | Synthesis, stability and optimized photolytic cleavage of 4-methoxy-2-nitrobenzyl backbone-protected peptides | |
| Botti et al. | Chemical Synthesis of Proteins and Circular Peptides Using Nα-(1-Phenyl-2-Mercaptoethyl) Auxiliaries | |
| FAUCHERE et al. | and Selective Deprotection in Peptide Synthesis | |
| Tatsu et al. | Caged Compounds and Solid‐Phase Synthesis | |
| JPH05506250A (en) | Inhibition of endothelin formation | |
| Ornelas | Photochemical synthesis of amino acid and peptide oxo-esters | |
| Vig et al. | Strategies for the Synthesis of Novel Head-to-Side Chain Cyclic Peptides: Application to Dynorphin A Analogs | |
| GB872332A (en) | Derivatives of amino acids and peptides, and synthesis of peptides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |